Diastereoselective Pauson-Khand reactions on aromatic substrates

被引：20

作者：

Blanco-Urgoiti, J ^{[1
]}

Casarrubios, L ^{[1
]}

Domínguez, G ^{[1
]}

Pérez-Castells, J ^{[1
]}

机构：

[1] Univ San Pablo, CEU, Fac CC Expt & Tecn, Dept Quim Organ & Farmaceut, Madrid 28668, Spain

来源：

TETRAHEDRON LETTERS | 2001年 / 42卷 / 19期

关键词：

D O I：

10.1016/S0040-4039(01)00446-4

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The synthesis of several natural products' frameworks is carried out by means of a diastereoselective intramolecular Pauson-Khand reaction promoted by molecular sieves. Diastereoselectivity is achieved only if a coordinating group is present at a convenient distance from the alkene moiety. Naphthalenes can be obtained directly under refluxing toluene conditions. (C) 2001 Elsevier Science Ltd. All rights reserved.

引用

页码：3315 / 3317

页数：3

共 16 条

[1] EFFICIENT SYNTHESIS OF 2-CHLOROINDOLE, 2-BROMOINDOLE, AND 2-IODOINDOLE
BERGMAN, J
VENEMALM, L
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (08) : 2495 - 2497
[2] Recent advances in the Pauson-Khand reaction and related [2+2+1] cycloadditions
Brummond, KM
Kent, JL
[J]. TETRAHEDRON, 2000, 56 (21) : 3263 - 3283
[3] A short synthesis of the potent antitumor agent (±)-hydroxymethylacylfulvene using an allenic Pauson-Khand type cycloaddition
Brummond, KM
Lu, JL
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (21) : 5087 - 5088
[4] A rapid synthesis of hydroxymethylacylfulvene (HMAF) using the allenic Pauson-Khand reaction. A synthetic approach to either enantiomer of this illudane structure
Brummond, KM
Lu, JL
Petersen, J
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (20) : 4915 - 4920
[5] Geis O, 1998, ANGEW CHEM INT EDIT, V37, P911, DOI 10.1002/(SICI)1521-3773(19980420)37:7<911::AID-ANIE911>3.0.CO
[6] 2-O
[7] INGATE ST, 1998, ORG P PREP INT, P123
[8] Synthesis of the spatane nucleus (cis-anti-cis-tricyclo[5.3.0.02,6]decane) using the Pauson-Khand reaction with a remarkable reversal in regioselectivity
Kowalczyk, BA
Smith, TC
Dauben, WG
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (05) : 1379 - 1389
[9] EFFECT OF COORDINATING LIGANDS ON THE PAUSON-KHAND CYCLOADDITION - TRAPPING OF AN INTERMEDIATE
KRAFFT, ME
SCOTT, IL
ROMERO, RH
FEIBELMANN, S
VANPELT, CE
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (16) : 7199 - 7207
[10] Synthesis of tricyclic aromatic compounds by the intramolecular Pauson-Khand reaction promoted by molecular sieves
Pérez-Serrano, L
Blanco-Urgoiti, J
Casarrubios, L
Domínguez, G
Pérez-Castells, J
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (11) : 3513 - 3519

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